There is something utterly magical about traveling with the whole family, but it’s not always easy to find the best destination for a multigenerational vacation. There are so many options—where can you go where everyone will have a great time?

I love watching both my parents and daughter discover new things, and, even more than that, I enjoy having the people I love the most all in one place. Of course, having an extra few sets of hands to wrangle the kids is an added bonus! But it can be hard to find a destination that appeals to everyone, so if you’ve decided to take a vacation as a family to celebrate a milestone birthday, retirement, graduation, or just to spend time together, I’ve put together a few of my favorite spots and travel tips that I’ve learned from years of multigenerational travel. Let’s get going!

Ocean Cruises

What:

An ocean cruise is probably the most traditional option when it comes to multi-generational travel, but it remains popular for a reason: there’s something for everyone! The kids can spend the day in the kids’ club, mom & dad can spend some time at the pool, and the grandparents can take a mixology class or relax on the pool deck. With wine tastings, trivia, scavenger hunts, and first release movies, you won’t run out of things to do unless you want to!

Where:

If you’re traveling with young kids, Disney Cruise Line is by far the best in the industry (and I’m not just saying that because I love Disney)! If you’re with children a little older, though, you may want to consider Royal Caribbean. Want to make this traditional vacation a little more adventurous? Consider a destination other than the Caribbean—despite the name, Royal Caribbean offers cruises to Alaska, the Mediterranean, and the Norwegian Fjords. With breathtaking views and engaging activities, there’s something for everyone to enjoy!

Beach Vacation

What:

Is anything better than beaches, family, and barbecue? Being from New England, I don’t know anyone who doesn’t remember spending time at the beach with their grandparents. But for my parents, a beach vacation always meant MORE work and less relaxation, and we spent half our vacation packing everything up for the house rental, cleaning, doing load after load of laundry, and grocery shopping. To make this a relaxing experience for everyone, look for resorts with villa style accommodations. Remember: a vacation is supposed to be a break from the busy! Let them do the laundry and clean the sandy toys.

Where:

One of my favorites is Hilton Head. There are some amazing beaches and even more amazing golf courses and spas there, and with many resorts offering kids’ clubs, the adults can actually enjoy some of those amenities! The city of Savannah is a short drive away and opens up a plethora of activities, adventures, dining options, and nightlife. Seeing as the cuisine is usually my driving point in decision making, this destination will always be at the top of my list.

River Cruise

What:

A river cruise is my favorite way to travel—floating down scenic coasts without the stress of constantly re-packing or coordinating travel times lets you explore a region in a unique and surprisingly stress-free way. Boarding your river cruise allows you to see multiple cities and towns without having to change hotels or spend hours on trains and buses. Plus, rivers were the highways that most of Europe was built on, so you can see dozens of bucket-list destinations without needing to plan separate trips!

This style of travel used to be reserved for retirees, but Disney has opened it up to families. Their partnership with AMA Waterways not only offers accommodations for families of 4 that you won’t find on other river cruises, but also itineraries that appeal to everyone. Imagine enjoying a wine tasting in France knowing that your kids are safe with trusted Disney cast members, having their own tasting (of pastries, of course)!

Where:

Adventures by Disney currently offers river cruises along the Rhine (Switzerland, France, Germany, and the Netherlands), the Rhone (Southern France), the Danube (Austria, Germany, Hungary), and the Seine (France.) While I personally love the Rhone, and I can’t wait to experience the Danube next year, I would recommend that families new to exploring Europe start with the Seine. It really immerses you in the French culture; it highlights history with visits to Normandy, art in Paris and Giverny (the home of Monet!), showcases the natural beauty of the region with an option for bike, hike or zipline adventures in Rouen, and, of course, cuisine all along the way with food tours, brandy tastings, cheese seminars, and more.

Dude Ranch

What:

I know what you’re thinking—”Christina, why would I take my family to a dude ranch?” It’s a great question, and I found myself asking it when I first became a mom, but hear me out—it’s actually a fantastic place for families! At any dude ranch, there’s something for everyone to enjoy, and most are all inclusive, making it simple to plan and budget for your next family vacation.

One of my favorite parts about a dude ranch destination is that you’re constantly surrounded by spectacular beauty, far from the noise and crowds of fast-paced cities, and it becomes hard not to reconnect. The BEST part is that there really is something everyone will enjoy…kids activities are numerous, teens will love adventuring on ziplines, rough waters, or horses, and adults can enjoy fine dining (yes, many dude ranches offer amazing 5 star restaurants!) and relaxation with fishing and spas.

Where:

I LOVE Jackson Hole WY. It’s not somewhere I ever had an interest in visiting, but I had to go for a work trip and fell in love. The majesty of the landscape paired with the realness of the people was just astonishing—it was genuine in a way no other place I have visited has ever felt. Adventures by Disney has two amazing itineraries in the Yellowstone area: one that features Jackson Hole WY and the other Bozeman MT. If neither are in your budget, consider a stay in downtown Jackson Hole!

Heritage Travel

What:

Heritage travel is essentially traveling to experience the places, artifacts, and activities that represent where we came from. Through storytelling, authentic experiences, and cultural tours, travelers can examine the life and times of their family’s history and the modern lifestyles of the region their ancestors came from. There is nothing more special than learning about your heritage with your family and the children that will continue your legacy.

Where:

I can’t really recommend a specific destination because this is based entirely on you. Right now, I’m planning on my own multi-generational heritage trip to Greece. My father has dreamt of visiting Greece for twenty years, and while I’ve been extremely fortunate to travel to the country my great grandparents emigrated from, my father hasn’t gotten the chance. I am so excited to watch him discover the history and culture of his father and share it with Annabelle!

Being from Boston, I plan a lot of heritage travel to Italy and Ireland as well. Both are amazing for the whole family, but I would recommend waiting until children are a little older to get the full experience out of Italy. Ireland is easy for kids of any age, and if you need a little push… check out the reasons you should bring your kids to Ireland!

Villa Rental

What:

If your family is scattered around the country and you’re looking for a way to slow down and enjoy each other’s company without constant tours and activities, you may want to consider a villa rental. 

Where:

With options for villa rentals available almost anywhere, it can be hard to choose a destination. My preference would be in the Tuscan countryside or provincial France where agrotourism (staying on a working farm) is growing. Being able to walk to the village to get fresh food or stop at the vineyard to enjoy their best vintage sounds incredible to me! It’s the perfect opportunity to really live like a local and grow to understand a new culture. 

These are just some of my personal favorite ways to travel with my family. Of course the possibilities are endless, and there are just so many incredible options for multi-generational groups! It can be overwhelming to coordinate multiple flights, interests, and everything that goes along with traveling with a group. The good news is: you don’t have to do it alone. I specialize in planning multi-generational vacations, and I can help you for no additional cost. Click the button below to schedule a complimentary vacation consultation, and let’s find a multi-gen vacation the whole family will enjoy!

In the meantime, check out Common Mistakes When Planning a Multigenerational Vacation to make sure you avoid some typical pitfalls.

Who is Christina?

Meet Christina Vieira: a Traveler, a Planner, and a Mom. She is also the owner of Showcase the World Travel, a modern travel agency that helps busy Moms take the vacation they deserve without adding “planning it all” to their to-do lists.  After all, Mom should get to enjoy their vacation, too.

She specializes in Disney, the Caribbean, Europe, and has helped dozens of families have magical vacations that they will always remember. She loves traveling with her four-year-old, Annabelle. Her favorite destinations include Walt Disney World, Wyoming, and Prague.